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18.2.9.2.7 Method 7: Cycloaddition Reactions Involving Carbon Diselenide

DOI: 10.1055/sos-SD-018-00070

Braverman, S.; Cherkinsky, M.; Birsa, M. L.Science of Synthesis, (200518246.

While 1,3-heterocumulenes do not comply with the definition of 1,3-dipolar compounds, they can undergo [3+2]-cycloaddition reactions with alkynes. In contrast to 1,3-dipolar compounds, which lead to saturated or unsaturated five-membered heterocycles, reactions of carbon diselenide with alkynes having electron-withdrawing substituents provide nucleophilic carbenes. These are unstable and dimerize to the corresponding tetraselenafulvalenes 540, usually as a mixture of cis- and trans-isomers (Scheme 270).[‌1114‌,‌1115‌] Carbon diselenide has been found to be more reactive toward alkynyl compounds than carbon disulfide.[‌1116‌]

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